EP0156280A3 - Process for the preparation of peptide intermediates poor in racemates, belonging to gonadorelin and gonadorelin analogues, their synthesis and intermediates obtained by this process - Google Patents

Process for the preparation of peptide intermediates poor in racemates, belonging to gonadorelin and gonadorelin analogues, their synthesis and intermediates obtained by this process Download PDF

Info

Publication number
EP0156280A3
EP0156280A3 EP85103106A EP85103106A EP0156280A3 EP 0156280 A3 EP0156280 A3 EP 0156280A3 EP 85103106 A EP85103106 A EP 85103106A EP 85103106 A EP85103106 A EP 85103106A EP 0156280 A3 EP0156280 A3 EP 0156280A3
Authority
EP
European Patent Office
Prior art keywords
denotes
gonadorelin
intermediates
preparation
obut
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP85103106A
Other languages
German (de)
Other versions
EP0156280A2 (en
EP0156280B1 (en
Inventor
Rainer Dr. Uhmann
Kurt Dr. Radscheit
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis Deutschland GmbH
Original Assignee
Hoechst AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to AT85103106T priority Critical patent/ATE50267T1/en
Publication of EP0156280A2 publication Critical patent/EP0156280A2/en
Publication of EP0156280A3 publication Critical patent/EP0156280A3/en
Application granted granted Critical
Publication of EP0156280B1 publication Critical patent/EP0156280B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S930/00—Peptide or protein sequence
    • Y10S930/01—Peptide or protein sequence
    • Y10S930/13—Luteinizing hormone-releasing hormone; related peptides

Abstract

The invention relates to a process for the preparation of peptides of the formula I U-A1-A213 A3-A4-A5-X (I) in which U denotes a urethane protective group, A1 denotes Trp or D-Trp, A2 denotes Ser, Ala or Thr, A3 denotes Tyr or Phe, A4 denotes Gly, the residue of a D-amino acid or the residue of a D-amino acid derivative, A5 denotes Leu, N-methyl-Leu, N-ethyl-Leu, Ser(But), Cys(But), Asp(OBut), Glu(OBut), Orn(Boc) or Lys(Boc) and X denotes OBut or A6-Pro-Y, where A6 represents Arg, Orn, Lys or homoarginine, and Y represents Gly-NH2, NH-NH-CO-NH2, (C1-C3)-alkylamino, cyclopropylamino, (C1-C3)-alkylamino which is substituted with hydroxyl or fluorine, or cycloalkylamino which is substituted with hydroxyl or fluorine, using tripeptides of the formula II, U-A1-A2-A3-OH, in which the residues are defined as above. The invention also relates to peptides of the formula II as intermediates in this process.
EP85103106A 1984-03-27 1985-03-18 Process for the preparation of peptide intermediates poor in racemates, belonging to gonadorelin and gonadorelin analogues, their synthesis and intermediates obtained by this process Expired - Lifetime EP0156280B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85103106T ATE50267T1 (en) 1984-03-27 1985-03-18 PROCESS FOR LOW RACEMA PRODUCTION OF PEPTIDE INTERMEDIATE PRODUCTS OF GONADORELIN AND GONADORELIN ANALOGUE SYNTHESIS AND NEW INTERMEDIATE PRODUCTS IN THIS PROCESS.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843411224 DE3411224A1 (en) 1984-03-27 1984-03-27 METHOD FOR THE RACEMATAR PRODUCTION OF INTERMEDIATE PEPTIDE PRODUCTS OF THE GONADORELIN AND GONADORELINANALOGA SYNTHESIS AND NEW INTERMEDIATE PRODUCTS IN THIS METHOD
DE3411224 1984-03-27

Publications (3)

Publication Number Publication Date
EP0156280A2 EP0156280A2 (en) 1985-10-02
EP0156280A3 true EP0156280A3 (en) 1987-10-21
EP0156280B1 EP0156280B1 (en) 1990-02-07

Family

ID=6231739

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85103106A Expired - Lifetime EP0156280B1 (en) 1984-03-27 1985-03-18 Process for the preparation of peptide intermediates poor in racemates, belonging to gonadorelin and gonadorelin analogues, their synthesis and intermediates obtained by this process

Country Status (10)

Country Link
US (1) US4691008A (en)
EP (1) EP0156280B1 (en)
JP (1) JPH0686478B2 (en)
AT (1) ATE50267T1 (en)
CA (1) CA1278650C (en)
DE (2) DE3411224A1 (en)
DK (1) DK170820B1 (en)
ES (1) ES8607342A1 (en)
HU (1) HU197928B (en)
IL (1) IL74703A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4608251A (en) * 1984-11-09 1986-08-26 Pitman-Moore, Inc. LHRH analogues useful in stimulating anti-LHRH antibodies and vaccines containing such analogues
US5191065A (en) * 1988-11-22 1993-03-02 Hoechst Aktiengesellschaft Process for the preparation of tripeptides
DE3839379A1 (en) * 1988-11-22 1990-05-23 Hoechst Ag METHOD FOR PRODUCING TRIPEPTIDES
DE19527574A1 (en) * 1995-07-28 1997-01-30 Basf Ag Process for the preparation of - (N, N-dialkyl) aminocaarboxamides
AUPO776897A0 (en) * 1997-07-09 1997-07-31 Csl Limited A method of achieving production gains in livestock and agents useful for same
AUPP807399A0 (en) 1999-01-08 1999-02-04 Csl Limited Improved immunogenic lhrh composition and methods relating thereto
DE10333042B4 (en) * 2003-07-21 2005-09-29 Clariant Gmbh Process for the preparation of cyclic phosphonic anhydrides and their use
CN112500455A (en) * 2020-10-12 2021-03-16 湖南津安生物科技有限公司 Method for synthesizing gonadorelin by polypeptide solid-liquid combination

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3915947A (en) * 1974-07-11 1975-10-28 Lilly Co Eli Des-{8 His{hu 2{b ,Gly{hu 10{b {9 -D-Ala{hu 6 {b LHRH ethylamide as an inhibitor of LHRH
US3963691A (en) * 1974-10-07 1976-06-15 Merck & Co., Inc. Synthetic antigens of luteinizing hormone releasing hormone
US4086219A (en) * 1975-10-29 1978-04-25 Parke, Davis & Company Nonapeptides and methods for their production
US4101537A (en) * 1977-04-07 1978-07-18 Parke, Davis & Company Octapeptides and methods for their production
US4272432A (en) * 1974-11-13 1981-06-09 American Home Products Corporation Claudogenic-interceptive nonapeptide
EP0041243A1 (en) * 1980-06-03 1981-12-09 Hoechst Aktiengesellschaft Nonapeptide, process for its preparation, composition containing it and its use
EP0056274A1 (en) * 1981-01-14 1982-07-21 Takeda Chemical Industries, Ltd. Indole derivatives and a method for production of peptides

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3953416A (en) * 1971-12-20 1976-04-27 Karl Folkers Synthetic decapeptide having the activity of the luteinizing hormone releasing hormone and method for manufacturing the same
FR2238700B1 (en) * 1973-07-24 1977-10-14 Takeda Chemical Industries Ltd
CS180644B2 (en) * 1973-09-29 1978-01-31 Takeda Chemical Industries Ltd Process for preparing nonapeptides
DE2438350C3 (en) * 1974-08-09 1979-06-13 Hoechst Ag, 6000 Frankfurt Peptides with a strong LH-RH / FSH-RH action, process for their production and pharmaceutical preparations containing them
GB1524747A (en) * 1976-05-11 1978-09-13 Ici Ltd Polypeptide
US4481190A (en) * 1982-12-21 1984-11-06 Syntex (U.S.A.) Inc. Nonapeptide and decapeptide analogs of LHRH useful as LHRH antagonists

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3915947A (en) * 1974-07-11 1975-10-28 Lilly Co Eli Des-{8 His{hu 2{b ,Gly{hu 10{b {9 -D-Ala{hu 6 {b LHRH ethylamide as an inhibitor of LHRH
US3963691A (en) * 1974-10-07 1976-06-15 Merck & Co., Inc. Synthetic antigens of luteinizing hormone releasing hormone
US4272432A (en) * 1974-11-13 1981-06-09 American Home Products Corporation Claudogenic-interceptive nonapeptide
US4086219A (en) * 1975-10-29 1978-04-25 Parke, Davis & Company Nonapeptides and methods for their production
US4101537A (en) * 1977-04-07 1978-07-18 Parke, Davis & Company Octapeptides and methods for their production
EP0041243A1 (en) * 1980-06-03 1981-12-09 Hoechst Aktiengesellschaft Nonapeptide, process for its preparation, composition containing it and its use
EP0056274A1 (en) * 1981-01-14 1982-07-21 Takeda Chemical Industries, Ltd. Indole derivatives and a method for production of peptides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF MEDICINAL CHEMISTRY, Band 22, Nr. 8, 1979, Seiten 935-943, American Chemical Society; G.W. MOERSCH et al.: "Synthesis and biological activity of peptide antagonists of Luliberin (Luteinizing hormone-releasing hormone)" *

Also Published As

Publication number Publication date
US4691008A (en) 1987-09-01
JPS60218399A (en) 1985-11-01
DE3575931D1 (en) 1990-03-15
EP0156280A2 (en) 1985-10-02
HU197928B (en) 1989-06-28
IL74703A (en) 1988-11-30
DK137085D0 (en) 1985-03-26
JPH0686478B2 (en) 1994-11-02
CA1278650C (en) 1991-01-02
ES8607342A1 (en) 1986-05-16
DK137085A (en) 1985-09-28
ATE50267T1 (en) 1990-02-15
IL74703A0 (en) 1985-06-30
ES541535A0 (en) 1986-05-16
DK170820B1 (en) 1996-01-29
DE3411224A1 (en) 1985-10-10
EP0156280B1 (en) 1990-02-07
HUT37445A (en) 1985-12-28

Similar Documents

Publication Publication Date Title
Rovero et al. Synthesis of cyclic peptides on solid support
HU903740D0 (en) Process for the production of new proteins
AU589674B2 (en) GRF analogs
YU200083A (en) Process for making hpgrf peptide
GB1523623A (en) Activity and process for their manufacture
US4003884A (en) Peptides having LH-RH/FSH-RH activity
MD1652G2 (en) Protein possessing the cytokin - type activity, recombinant DNA-codifyer for such protein, transformed cells and microorganism, expression vector, process for protein obtaining and remedy containing such a protein
KR870007203A (en) Methods for making peptides
EP0156280A3 (en) Process for the preparation of peptide intermediates poor in racemates, belonging to gonadorelin and gonadorelin analogues, their synthesis and intermediates obtained by this process
NZ198626A (en) Peptides and pharmaceutical compositions
Wang et al. Preparation of protected peptide intermediates for a synthesis of the ovine pituitary growth hormone sequence 96-135
EP0452514B1 (en) Peptide and process for preparing cyclic peptide
US4491541A (en) Peptides
GB2130590A (en) Peptides
PL316069A1 (en) Novel derivatives of biotin and method of obtaining them as well as pharmaceutic preparation and method of preparing same
GB1465235A (en) Process for preparing peptides
EP0056274A1 (en) Indole derivatives and a method for production of peptides
Naithani et al. SELECTIVE N-AND C-TERMINAL ELONGATION AT A1 AND B30 OF INSULIN: NEW APPROACHES TO PROINSULIN RELATED CONVERSION INTERMEDIATES
KR890002234A (en) Peptides with vasodilation, sodium excretion and diuretic activity, preparation method thereof, preparations containing same, and use thereof

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): AT BE CH DE FR GB IT LI LU NL SE

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE CH DE FR GB IT LI LU NL SE

17P Request for examination filed

Effective date: 19871130

17Q First examination report despatched

Effective date: 19881020

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE FR GB IT LI LU NL SE

REF Corresponds to:

Ref document number: 50267

Country of ref document: AT

Date of ref document: 19900215

Kind code of ref document: T

REF Corresponds to:

Ref document number: 3575931

Country of ref document: DE

Date of ref document: 19900315

ITF It: translation for a ep patent filed

Owner name: ING. C. GREGORJ S.P.A.

ET Fr: translation filed
GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
ITTA It: last paid annual fee
EPTA Lu: last paid annual fee
EAL Se: european patent in force in sweden

Ref document number: 85103106.2

REG Reference to a national code

Ref country code: CH

Ref legal event code: PUE

Owner name: HOECHST AKTIENGESELLSCHAFT TRANSFER- AVENTIS PHARM

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

NLS Nl: assignments of ep-patents

Owner name: AVENTIS PHARMA DEUTSCHLAND GMBH

REG Reference to a national code

Ref country code: FR

Ref legal event code: TP

REG Reference to a national code

Ref country code: GB

Ref legal event code: 732E

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20040218

Year of fee payment: 20

Ref country code: AT

Payment date: 20040218

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20040219

Year of fee payment: 20

Ref country code: GB

Payment date: 20040219

Year of fee payment: 20

Ref country code: FR

Payment date: 20040219

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20040220

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: LU

Payment date: 20040305

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20040331

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20040401

Year of fee payment: 20

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20050317

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20050317

Ref country code: CH

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20050317

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20050318

BE20 Be: patent expired

Owner name: *AVENTIS PHARMA DEUTSCHLAND G.M.B.H.

Effective date: 20050318

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

NLV7 Nl: ceased due to reaching the maximum lifetime of a patent

Effective date: 20050318

EUG Se: european patent has lapsed
BE20 Be: patent expired

Owner name: *AVENTIS PHARMA DEUTSCHLAND G.M.B.H.

Effective date: 20050318